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Chemistry of Natural Compounds

, Volume 47, Issue 6, pp 921–924 | Cite as

Synthesis of fluorine-containing betulin esters

  • T. S. Khlebnikova
  • Yu. A. Piven′
  • V. A. Nikolaevich
  • A. V. Baranovskii
  • F. A. Lakhvich
  • Nguen Van Tuen
Article

28-O-Fluoroacylbetulins were synthesized via acylation of betulin by fluorocarboxylic (perfluorobutyric, perfluorooctanoic, 3-fluorobenzoic, perfluorobenzoic) acid chlorides in CHCl3 in the presence of Py. 3,28-Di-O-fluoroacylbetulins were prepared by treatment of betulin with fluorocarboxylic (trifluoroacetic, pentafluoropropionic) acid anhydrides in Py in the presence of 4-dimethylaminopyridine. 3,28-Di-O- (3-fluorobenzoyl)betulin was obtained from acylation of betulin by 3-fluorobenzoic acid in CH2Cl2 in the presence of N,N′-dicyclohexylcarbodiimide and 4-dimethylaminopyridine whereas acylation by perfluorobutyric acid under the same conditions gave 28-O-perfluorobutanoylbetulin.

Keywords

betulin acylation fluorine-containing betulin esters 

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Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • T. S. Khlebnikova
    • 1
  • Yu. A. Piven′
    • 1
  • V. A. Nikolaevich
    • 1
  • A. V. Baranovskii
    • 1
  • F. A. Lakhvich
    • 1
  • Nguen Van Tuen
    • 2
  1. 1.Institute of Bioorganic Chemistry, National Academy of Sciences of BelarusMinskBelarus
  2. 2.Chemistry Institute of the Viet Nam Academy of Sciences and TechnologyHanoiViet Nam

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